Regiospecific synthesis of 3-alkyl-4-hydroxybenzimidazoles as intermediates for an expedient approach to potent EP3 receptor antagonists

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• 作者：Wayne Zeller ; Alex S. Kiselyov ; Jasbir Singh
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：10 March 2010
• 年：2010
• 卷：51
• 期：10
• 页码：1380-1382
• 全文大小：247 K

文摘

Regiospecific construction of 3-alkyl-4-hydroxybenzimidazoles is detailed. The synthetic route involves a novel O- to N-acyl transfer reaction to address the observed exclusive O-acylation of 2-amino-3-nitrophenol starting material. This efficient route provides the targeted 3-alkyl-4-hydroxybenzimidazoles in good yields, in five steps, without the use of chromatographic purification. These key intermediates were subsequently elaborated, as shown, to provide acylsulfonamide-derived potent EP₃ receptor antagonists.